Pokemon Truth or Dare!
by Anna10327
Summary: WARNING: Will contain AdvanceShipping, GymShipping, RocketShipping, and CavalierShipping. Someone help me come up with a name with the shipping for Max & Serena, because the story involves that ship too! It's my first nevermet ship, don't judge. It's so elusive it doesn't have a name.
1. Introduction

A girl with brown eyes, brown hair, and a gray shirt with starting Kanto Pokémon appeared.  
"Hello everyone, I'm Anna10327! But please, call me Anna. I kidnapped Ash Ketchum, Misty Henderson, Brock Harrison, Gary Oak, Dawn Alexis, May & Max Dawson, James Rochester, and Jessie Morgan and brought them here for our own truth or dare!" **(A/N: Misty, May, Max, and Dawn don't have mentioned last names, so the last names I used for them are what I think they are) **  
"Wait, you kidnapped us?" a voice asked. It was Ash.  
"Darn, they're awake. And yes, I did. I had no choice. This isn't your cliché truth or dare story. You guys can do anything in this story, as long as it stays it the T rating!" Anna said.  
"T rating? What does that mean?"  
"T stands for Teen. This truth or dare will contain sexual content and cussing." Anna explained, winking at Ash on the sexual content part, since Anna was planning stuff for him to do with a certain brunette girl, and it wasn't herself, though she did think Ash was cute. "First, let's go over rules. There will be survival challenges at some points, but no one will actually die. These guys will go in groups. Ash, you'll go with May. Brock, you'll go with Misty. James, you'll go with Jessie. And Gary, you'll go with Dawn." Anna removed the microphone from her mouth and whispered to the audience, "I paired them up into couples that I ship. I know, it's crazy to ship Gary with Dawn. But I had to do something, right? Plus I'm curious about how that would work out."  
"Why are you putting us into groups of twos? Not that I'm complaining, I like being paired with Ash." May blushed.  
"I'm not telling you. I might be just a fan of your show, but I know secrets you refuse to believe. Just deal with it, I'm pairing you with the person you work best with." Anna lied.  
"But why put me with someone I don't know?" Dawn asked.  
"Don't question my judgment, I barely know you either! But I put you in the story for the sake of the readers!" Anna shouted. "Anyways, can we get started? I have some stuff I want to ask. Okay, Brock, you're first. Truth: Why are you such a perv?"  
"I am not a pervert, you're the pervert. I see you staring at a place you shouldn't be staring at." Brock said. Anna blushed.  
"I'm sorry, you're just cute."  
"Well, anyways, the true reason I'm even close to that is very private. If you think I'll tell this many people why, you must be stupid." Brock explained.  
"Just whisper it in my ear. I'll turn off the microphone, I promise. And I won't tell anyone, not even my best friend, Abbie." Anna promised. Brock sighed. So he did it and Anna gasped.  
"I knew it all along! Well, I might tell Isaiah to prove him wrong. He's so much of an idiot and doesn't think that's the truth. I promise, I'll only tell Isaiah." Brock was blushing. "No, you're not telling anyone, unless you want to die a painful, slow, and excruciating death."  
"Geez, I won't. Isaiah is not even that good of a friend to me that I'd tell secrets to." Anna backed away from him. "Okay, let's go on. Misty, I have a dare for you. You sing Invisible by Taylor Swift to you-know-who. It's the guy you love."  
"No." Misty said.  
"Misty, come on. Do it for the Vine!"  
"I ain't gonna do it!"  
"Do it for the Vine!" Ash, May, Dawn, and Max chimed in.  
"I ain't gonna do it!"  
"Do it for the Vine!" This time, Brock, Gary, and the audience chimed in.  
"Okay, fine, maybe next chapter after other truths and dares." Misty threw in the towel.

* * *

**PM me or review for your truths and dares! I won't accept anything going over the T rating. By the way, I'm Anna, Abbie is my real life best friend, and Isaiah is my idiot PokeShipper friend IRL.**


	2. Smosh & Romance!

"Okay, guys, no one is sending truths or dares. I'll come up with some. You guys in the audience have to PM me requests now, because of a little parasite programmed to get every story deleted. Oh, one reviewer said that Max has no partner. My bad!" Anna said.

"Well, do I have a partner now? Pair me up with someone, please! Make it a cute girl, I want to kiss her and show Brock that I'm more like him than he thinks." Max explained.

"Yes, you do, Max. Meet Serena, Ash's friend from Kalos! She's 10, but that shouldn't matter. That's nothing compare to the age difference of Delia Ketchum and Professor Oak. Love knows no age, got that, Max? You too, Brock the dense?" Anna asked. Brock nodded, not getting Anna's gist.

"Okay. Serena's fine. If we were older, I would take her to my bedroom." Max said.

"Oh my god, Max, you sure are twisted for a cute and innocent 8-year-old." Anna said, facepalming.

"Did you just call me cute?" Max inquired. Anna blushed.

"Yes. Not as cute as Ash & Brock, but you're getting there. You're just irresistible!" Anna confessed. When Anna saw that May was looking at her weirdly, and Ash looked disgusted since Anna had a crush on him, she changed the topic. "Okay, Ash Ketchum, Truth or Dare?"

"I'll do both. Dare first." he said. Anna had a smirk wipe across her face.

"Okay. I dare you to let me kiss you on the cheek. I'm saving the lips for another girl." Anna said. She winked at May.

"Fine. But can I go wash my face afterwards?" Ash asked.

"Of course, Ashy-boy, but let May get rid of any stains by mouth..." Anna suggested, winking at Ash this time. Anna leaned closer to him, and pecked his cheek. Ash ran away from her.

"Oh my god, that was horrible! I only wanted to be kissed by one girl!" he screamed.

"Is it me?" May asked, trying to get Ash to kiss her already.

"So, what's the truth?" May asked. She was holding Ash in her arms, comforting him. May had spoken for Ash, since he was far too nervous to say anything.

"Okay, here it is. Ash, please point at every girl in this room you have a crush on right now. Two fingers for obsession, 1 finger for Brock-like crush." Anna explained. He finally decided to calm down. Ash pointed two fingers at May, and one to Serena. Serena and May blushed.

"May, Dawn, Brock, Misty, Gary, Max, Serena, do the same thing. I wanna see you be brave!" Anna dared, singing the last sentence. May pointed two fingers to Ash, Dawn had pointed all of her fingers to Gary, Max pointed two at Serena, Serena pointed two to Ash & Max (yeah, I decided to do that, it's crazy, I know), Gary pointed two to Dawn and one to Misty, and Brock pointed two at Misty.

"Aw, I knew it all along! I wasn't expecting Gary to point a finger at Misty though; luckily he is obsessed with Dawn. Oh, Serena, I think you should choose Max. Trust me, he's an awesome kid. There's only a 2-year-age differences between you guys. I don't need Max, there's a 3 year difference between me and him. Actually, almost 4." Anna explained, being Max's wingman, or girl in this case. "Oh yeah, I have another dare! It's for all of you guys! I dare you all to watch New Pokémon Crossovers by Smosh!"

"Who's Smosh?" Brock asked.

"You know you guys are your own show, and Smosh loves your show. They're two guys named Anthony Padilla & Ian Hecox who makes lots of videos about Pokémon. Anthony pretends to be Ash in most Pokémon videos, like this one. Oh, just a warning, Ash, you're romantically linked to Misty in this vid." Anna said. Ash's cheeks turned green, and he vomited all over Misty.

"Ash Ketchum! You electrocuted my bike and turned it into ashes, now you puke on my head! Brock must think I look ugly now." Misty cried. Brock blushed, literally all over.

"No, Misty, you look beautiful no matter what," Brock said. Anna changed the subject immediately before the show turned into an orgy started by Brock.

"Okay, so let's start the video. Ian is the one with the bowl haircut and beard, Anthony is the one with emo girl hair. It's funny to me, but I really want to see Ash & Misty's reactions to the spoof of a romantic movie I don't know the name of. And Ash looks totally sexier when Ash cosplays as him, you'll agree with me, May." Anna said.

_"So, wait, you're telling me I'm not the father?" Ash asked Misty, his pregnant girlfriend.  
"Sorry, but no. It is another." Misty confessed.  
"Damn it, Misty! I've saved you from Team Rocket a dozen times, the least you can do is tell me who the father is!"  
"I'm sorry, I can't!" Misty said.  
"Damn it, Misty!" Ash walked out crying.  
"We're safe now... He's gone..." Misty said. The real father of Misty's offspring appeared from under the blanket, a Magikarp.  
"Karp!" it shouted. _

"Anna, can I just pretend that the Magikarp was really Brock? I can't handle bestiality, and I would never make love to Ash!" The real Misty said. Anna nodded, and continued the video.

_"Don't worry, we have an even more romantic idea..." Ian said. A title card saying 'Game of Pokémon' came across the screen.  
"Sleep with me and give me dragon babies," some white haired lady pleaded to a Charizard.  
"Uh uh!" it snapped.  
"Do it, or I'll fu**ing cut your head off!" the lady said. Later that night, Charizard was having sex reluctantly with the unnamed lady._

Ash broke into tears from laughter, along with Dawn & May. "What if that were my Charizard?" he wondered.

"That would make it funnier!" Dawn said.

"Man, I love these guys!" May said, still laughing.

"Misty is still scarred from the Days of Our Pokémon part. It's okay, Misty, it wasn't real. But here's something that is real." Brock assured, kissing Misty on the cheek. A smile spread onto Misty's face.

"Am I the only one who saw that coming?" Anna asked. Everyone else, including the audience, shook their heads.

* * *

**I don't have the time to write about every part of New Pokémon Crossovers. If you haven't seen it and want to watch the rest, go to YouTube and search in 'new pokemon crossovers smosh'. **


End file.
